去氢吴茱萸素 | 24099-25-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 去氢吴茱萸素
• 中文别名: 4-哌啶甲酰胺,N,2-二甲基-,(2R-顺)-(9CI)
• 英文名称: anhydroevoxine
• 英文别名: 7-[(3,3-dimethyloxiran-2-yl)methoxy]-4,8-dimethoxyfuro[2,3-b]quinoline
• CAS: 24099-25-0
• 化学式: C₁₈H₁₉NO₅
• 分子量: 329.353
• InChiKey: ZFZSGUNUXDDUOD-UHFFFAOYSA-N

物化性质

• 熔点：
  133-134 °C
• 沸点：
  467.3±40.0 °C(Predicted)
• 密度：
  1.245±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  66.2
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  去氢吴茱萸素 在 silica gel 作用下， 反应 72.0h， 以62.8%的产率得到7-(3-anilino-2-hydroxyprenyloxy)-8-methoxydictamine
  参考文献：
  名称：

  A rotameric tryptamide alkaloid from the roots of Vepris lecomteana (Pierre) Cheek & T. Heller (Rutaceae)

  摘要：

  A rotameric tryptamide alkaloid (1a-1b) was isolated from the methanolic extract of the roots of Vepris lecomteana together with the known compounds anhydroevoxine (2), lecomtequinoline C (3), evoxine (4), N-methylflindersine (5), evoxanthine (6), hesperidin, lupeol, beta-sitosterol and stigmasterol. The previously not reported 7-(3-anilino-2-hydroxyprenyloxy)-8-methoxydictamine (2a) was obtained by opening the epoxide of anhydroevoxine (2). The structures of above compounds were determined by comprehensive spectroscopic analyses of 1D and 2D NMR, EI-/ESI-MS, X-ray crystallography and comparison with the reported data. At room temperature, H-1 and C-13 NMR spectra show two rotamers (1a and 1b) with integrated intensities of 2/3, whereas at around 60 degrees C, only the 1b conformer was observed. Furthermore, the crystal structure of 1 was determined by the direct method of single crystal X-ray diffraction. The suggested biosynthesis for the formation of the new rotameric tryptamide alkaloid 1 is presented. Some of the isolated compounds (1, 2 and 2a) were tested in vitro against bacteria, resulting in weak for (1 and 2) to moderate activity for (2a) against Micrococcus Mulls and Escherichia coli with MIC values of 15.3 and 15.3 mu g/mL, respectively.

  DOI：

  10.1016/j.fitote.2019.03.028